Synthesis 2006(11): 1760-1762  
DOI: 10.1055/s-2006-942364
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Unexpected Product in the Synthesis of Bis(2-iodo-3-thienyl)methanol: Characterisation of Bis[bis(2-iodo-3-thienyl)methyl]ether

Ethan D. Goddard-Borger, George A. Koutsantonis*, Phil A. Schauer, Brian W. Skelton, Allan H. White
Chemistry, M313, School of Biomedical, Biomolecular and Chemical Sciences, Faculty of Life and Physical Sciences, The University of Western Australia, 35 Stirling Hwy, Crawley, WA 6009, Australia
Fax: +61(08)64887247; e-Mail: gak@chem.uwa.edu.au;
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Publikationsverlauf

Received 23 December 2005
Publikationsdatum:
05. Mai 2006 (online)

Abstract

Following a literature procedure for the preparation of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one, it was found that insufficient attention and control of the reaction temperature led to the formation of bis[bis(2-iodo-3-thienyl)methyl]ether, via a yet to be determined mechanism. Though the synthetic route to the desired ketone has previously been extensively investigated, and numerous byproducts isolated and characterised, this coupled ether product has not been previously reported nor foreseen. Presented herein are the synthesis and full characterisation of the new ether compound.

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Brzezinki, J.; personal communication.